Kentucky Derby Style: She Belongs.

About a month ago, I shot Kentucky Derby-style content on a private jet. (Definitely NOT my jet!) The photo shoot was part of an auction package that some friends and I won on Gentlemen for MS, a fundraiser here in Louisville for the National MS Society. While I know that not everyone would be excited about a fashion photo shoot in pajamas (as the brilliant Succession say the kids), I saw it as an opportunity to take some fun photos with people I enjoy in an environment I wouldn’t normally have access to. Do it for the content, baby!!! (And time with friends, of course! It was so much fun.)

Marginal note: I’m on the planning committee Gentlemen for MS And you should definitely come to the festivities this year. Or sponsor! Or donate a high value item/package that we can use in our live auction! For any of these, feel free to contact me at any time.

It’s this photo shoot I was referring to in my last post about the experience of trying to find an outfit that truly reflected how I wanted to look. The challenge of reconciling my vision and the very, very limited plus size options available was infuriating. I hope you read that article if you haven’t already. It will give you a much deeper insight into my mindset when facing this experience, as well as the transformative power of clothing.

I use clothing and style as a way to show myself that I belong. That I am someone worth seeing. That I am more than my size. That I can stand out and not shrink. I can take up space.

It’s more than just a dress.

When I saw the photos from the shoot, it was like I was looking at another person. I looked at her and she seemed she belonged. While fashion is subjective, I thought the person reflected in the photos was elegant, sophisticated, full of confidence and someone who understood style. You might see these photos in a Derby editorial or on a “what they were wearing” list. Then I realized that it seemed very new to me because I didn’t remember having seen plus-size bodies in this context. When you’re my size, you notice these things. It’s like seeing a unicorn. And who doesn’t want more unicorns in the world?!

Note: As I am about to delve deeper into the social/fashion aspects of this event and everything surrounding it, I recognize that there are many complex issues at play. Privilege abounds in much of this brouhaha, and there are situations of class, race, and ethics that are intertwined in a big knot that also has a tremendous economic impact for our city.

For those unfamiliar with the fashion spectacle that is the Kentucky Derby: here in Louisville, it’s not just about the fastest two minutes in sports. The first Saturday in May is the *main event*, but it’s also the reason for the season.

Yes, season.

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Events in the city revolving around the Kentucky Derby begin in early March, 2 months before race day. Many people who participate don’t even go to the races, but it is the ideal time for social events. A time to see and be seen. Those interested in the holidays begin scheduling parties, fashion shows, fundraisers, and more even before March. Hatmakers are working feverishly to meet demand, and boutiques and brands are revealing their Derby-related products and styles that are worthy of the show. It’s all very edgy, which makes it fun for someone like me who loves to express herself through fashion. It’s also fun to show the rest of the world that there are multitudes in Kentucky beyond Kentucky Fried Chicken and the stereotype that we don’t wear shoes.

It’s glitz, glamour, lots of bourbon, and a reason to wear fantastic headpieces. It’s so fun to have a reason to wear artwork on your head. I think we should have more of that everywhere. But of course, I love any reason to personalize.

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If you look at fashion editorials, local or national, that are considered the epitome of Kentucky Derby fashion, you won’t find many visibly plus-size women. This year, the local lifestyle magazines and their beautifully produced Derby fashion editorials did not include anyone I perceived to be over a size 14. Browsing the galleries of Town & Country, Vogue, Southern Living and Garden & Gun turned up hundreds of photographs. with maybe 5 people above size 14, but none that I would classify in the 18+ size range. Considering that 67% of American women are size 14 or larger, math isn’t math.

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Locally, the lack of representation could be because stores that offer styles for models don’t carry plus sizes. Nationally, coverage consists primarily of street-style photographs of the event organized into large photo galleries with headlines such as “The Best Fashion at the Kentucky Derby.” Given the 155,000 people who attended, I can’t help but wonder if this exclusion is due to anti-fat bias. I know there are many stylish women of all sizes who attend the Kentucky Derby. If, in the eyes of the editor who compiles the selected images, big does not equate to fashionable, they will not be in the gallery.

It may not be an intentional exclusion, but when we operate in a world of conventional beauty standards where smaller is perceived as more attractive and the beauty creators of the media world are in charge of curating what they show, it feels like an exclusion. choice.

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Also something very specific to me: the “influencer” invitations and partnerships around this time of year can reek of high school popularity contests. I guess this happens with all associations throughout the year, but around Derby season, it’s very noticeable when everything happens within a 10 mile radius of where I sit. At home. Without heels. Maybe sleeping. Or reading a book. So maybe it’s a win for me after all! 🤷🏻‍♀️

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There are many times where I avoid places because I think I probably won’t fit in. Or even I won’t fit, because size accessibility is an issue. It’s gotten better over the years, but there are always hills and valleys in the search for confidence. Visual representation may seem trivial, but there is a lot of power in seeing someone like you, or your friends and family, represented. We could all use a reminder that we belong.

Many thanks to Doctor Hat, Ilana Kogan, for providing the absolutely stunning fascinator and for being part of the fun day, along with my friend and fellow Misters for MS committee member, Debra de Debra Locker Group.

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Ilana, Debra and I (obviously!)

thanks to Crew aviation aircraft for the generous donation of this auction package to Misters for MS, including the skills of the immensely talented Andrea Hutchinson behind the camera. Cassie’s Makeup I did a great job with my makeup!


Dress, ELOQUII (Also available in other colors)
Fascinating, doctor hat – It has really amazing pieces!
Old Shoes – similar
Earrings, Lele Sadoughi
Sunglasses, DIFF glasses (from my HSN collaboration here)

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Photography: Andrea Hutchinson
Make up: Cassie’s Makeup
Location: Crew aviation aircraft

Want more plus size Kentucky Derby outfits and style? I have a lot in my files!

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